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Holiday Rentals nearby Simi Winery

16275 Healdsburg Ave, Healdsburg, California 95448-9075
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    ₹ 51,302 Average
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    Travellers to Healdsburg are booking October dates now. Secure your holiday home today, and have the perfect trip.
    All 24 Rentals in Healdsburg
    Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views1 / 32
    (16)Very good
    3.3 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    VineHaven / Spa, Gardens, & Spectacular Vineyard Views1 / 21
    (5)Excellent
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!1 / 25
    (5)Excellent
    1.7 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly1 / 25
    (3)Excellent
    7.0 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2016
    the house is fabulous and the location is perfect.minutes to town and lots of wineriespeaceful setting and cool clean house
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    About this property
    Location, location location! Perfectly situated only 3 miles (a 5-7 minute drive) from the charming and historic Healdsburg Plaza, this fabulous, custom three-bedroom home abounds with special eco-friendly features. You will be wowed by this modern home’s beautiful open-beamed cathedral ceiling,...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    4.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
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    • Balcony
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    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully located, perched just above the Russian River, on S. Fitch Mountain, this vintage 1927 river home has been beautifully renovated and modernized with central heat/AC, new dual-paned windows, high open-beamed ceilings, and all the modern conveniences while still maintaining its vintage...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Beautiful mountain top wine retreat in Healdsburg!1 / 26
    (1)Excellent
    3.9 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Grill
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    • Housekeeping Included
    • Central Heating
    • Mountain Views
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 June 2015
    I would definitely recommend this property. My wife and I stayed there with friends for a wine country holiday. The house seems recently remodeled with many seating areas both...
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    About this property
    Our home is a perfect starting point to Alexander Valley and Dry Creek wineries and a short walk to the banks of Russian River where you can float, kayak, paddle board or just lay in the sun. Nested on Fitch Mountain, our home is in the heart of nature. You are close enough to downtown Healdsburg...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!1 / 25
    (4)Excellent
    2.0 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shaded by a 100-year-old oak tree, this very special home ‘lives’ on 30 vineyard acres and is off Dry Creek Road, just one mile west of the north end of charming, upscale, historic, Healdsburg in the heart of Sonoma County’s Wine Country. Newly renovated, this 3 bedroom/2 bath, Ranch House with...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    5.4 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    * TurnKey photo-verifies this home is professionally cleaned with products approved by the EPA for use against COVID-19. * PROPERTY OVERVIEW A lavish retreat for the ultimate group getaway, this stunning 3BR/3BA home with a guest suite is hedged by expansive vineyards and mature trees. Spend an...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    3.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Mountain Views
    • Patio
    • Cable/satellite TV
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    • Central Heating
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    River View Lodge appeals to guests with its spectacular riverfront setting, spacious river view deck, charming décor, exceptionally comfortable beds and linens, outstanding cleanliness, and quality amenities. River View features private river access, and includes kayaks, paddles and life jackets....
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3.4 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Housekeeping Included
    • Waterfront
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    • Mountain Views
    • Patio
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy Riverfront Home with Peace and Seclusion awaits you in the heart of Healdsburg. Tucked into one of the best locations on Healdsburg's Riverfront awaits this upscale cottage. Open Floor Plan with lots of Natural Light and Large Expansive Deck. Redwood River House is a well maintained 2...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4.3 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to heavenly Healdsburg and Hilltop's Vista Villa! This gated 2-bedroom, 2-bath luxury Tuscan inspired villa is located only 3 miles from the historic Healdsburg plaza on one hillside acre near the top of the east side of Fitch mountain and is the only home this close to the top! This...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.8 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Hot Tub
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning gated modern ranch house is nestled on one acre among the vineyards, and very well located at the north end of Healdsburg on Alexander Valley Road. Just remodeled, professionally decorated and furnished, this single story, 2000 sq. ft., 3 bedroom, 2.5 bath home sits under the shade of...
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.9 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Internet Access
    • Secure Parking
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your vacation in the heart of Healdsburg, CA at the Moorish-inspired Cypress House. Beautiful tiles, an interior courtyard, and an incredible view of downtown and beyond from the top floor terrace make this property unique to wine country. Located at the edge of a small shopping center, it...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.2 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly remodeled vacation rental home is wonderfully located less than 8 minutes north of downtown Healdsburg. It is nestled on the rolling hills of Dry Creek Valley with views looking towards Alexander Valley. Recently refreshed with stylish furnishings, fixtures and lighting system, the home...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    2.7 kilometres from Simi Winery
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The cottage is a well-appointed, stand-alone unit with a private gate and entrance which provides an ideal retreat for touring the Sonoma and Napa wine country. Located in a garden setting 5 blocks from the Healdsburg Plaza in the central, historic district, it is adjacent to a 2-story, 1880's...
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    Healdsburg, Sonoma County
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    7.1 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just Five minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    2.9 kilometres from Simi Winery
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Charming 2 bedroom 1880's Cottage is the perfect wine country getaway for 4. Just 2 blocks from the historic Downtown Plaza, Restaurants, Boutiques and Wine Tasting. The newly remodeled contemporary furnished interior is well appointed for you getaway needs. Living Loom, Dining area, Kitchen...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    2.2 kilometres from Simi Winery
    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Hot Tub
    • Grill
    • Wi-Fi
    • Terrace
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Residence at Comstock Wines is located on our 17 acre Estate Vineyards and was completed in 2016. The Residence boasts four stunning Master Suites, each offering private entrance, vineyard view terrace, gas fireplace, OrganicPedic beds, 1500 thread count linens, shower with vineyard view window...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
    0.4 kilometres from Simi Winery
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Sauna
    • Washer
    • DVD Player
    • Grill
    • Mountain Views
    • Hot Tub
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hello wonderful Guests! We are happy to share our beautiful home that we have built from scratch 8 years ago. We have put much thought and consideration into each aspect of the home. We have children, so we have made this home very family friendly. Children simply love the home and grounds with...
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    Healdsburg, Sonoma County
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    2.8 kilometres from Simi Winery
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Central Heating
    • Balcony
    • Mountain Views
    • Grill
    • DVD Player
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2nd floor: 11 foot ceilings. Beautiful, gourmet kitchen with stunning views. Kitchen is equipped with a Thermador 6 burner (and grill) gas stove top and double electric oven. Butcher block counter tops. Dishwasher, Professional quality knives and cookware. Large microwave. Spacious walk-in pantry....
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    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    3.1 kilometres from Simi Winery
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Downtown Healdsburg Victorian Cottage: recently remodeled, one story, open floor plan, chefs kitchen, indoor-outdoor living, covered porch, and hot tub. Easy walk to Plaza, restaurants, wine tasting lounges, movies, performing arts theater, art galleries, and boutique shops. At the Center of Dry...
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    Healdsburg, Sonoma County
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.1 kilometres from Simi Winery
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Washer
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alexander Valley Retreat Immerse yourself in the spectacular wine country of the Alexander Valley at this beautiful estate on 10 private, sun-drenched acres in Healdsburg. This 2,400-square-foot home has been lovingly maintained, offering high ceilings, crown moldings, oak floors, and a gourmet...
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    Location Information
    Healdsburg, Sonoma County
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    7.3 kilometres from Simi Winery
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Armida Vineyards Cottage Escape to your very own piece of California wine country at this Healdsburg vacation rental, where you'll enjoy sweeping vineyard views and an ideal location for exploring one of the region's most beloved towns. Dramatically situated in the middle of a 12-acre vineyard,...
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    Windsor, Sonoma County
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2.5 kilometres from Simi Winery
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This stunning vineyard estate home is perched on a hill with spectacular 360-degree vineyard views of Geyser Peak, Alexander Valley and the Dry Creek hills. This spacious home features a lovely pool & spa, gourmet kitchen, wrap-around veranda, vaulted ceilings with crown moldings, hardwood...
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    Geyserville, Sonoma County
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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